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APC candidate Adebayo Adelabu, who lost the March 2019 Oyo governorship election to Makinde, petitioned to overturn the result. The Governorship Election Tribunal dismissed his petition, but the Court of Appeal then set aside the tribunal's judgment as perverse in November 2019 — without ordering a re-run — creating confusion over Makinde's status weeks before the case reached the Supreme Court.

The Supreme Court unanimously found the Court of Appeal's majority judgment a miscarriage of justice and restored the tribunal's original decision upholding Makinde's election, resolving the dispute in his favour roughly seven months into his first term.

Local government chairmen and councillors elected on the APC platform, who were dismissed by Makinde on his first day in office in May 2019 before their tenures had formally expired, sued for their unpaid salaries and entitlements for the remainder of their terms.

The Supreme Court ruled against the state, ordering payment of roughly ₦4.9 billion. When ₦3.4 billion of that sum remained unpaid, the Court of Appeal in 2023 additionally fined Makinde and six co-respondents ₦50 million in damages for disregarding the judgment, with the panel describing the conduct as disrespectful to the judicial system.

The Nigeria Union of Pensioners sued the state government, seeking payment of ₦42.3 billion in unpaid gratuities and pensions owed to retired primary school teachers and local government staff, accumulated substantially under the previous administration.

The court had earlier ordered monthly payments of ₦250 million toward the arrears. Makinde's administration increased the monthly allocation well beyond that order — to roughly ₦500 million shortly after taking office and around ₦1 billion in later years — representing substantive, if gradual, compliance with the underlying obligation, even though the full historical debt was not immediately eliminated.

Creditors pursuing outstanding multibillion-naira debts obtained a court order to place a lien on Oyo State Government bank accounts, escalating pressure on the administration to resolve outstanding contractor and judgment debts.

The order disrupted normal state financial operations until the underlying debts were addressed, illustrating the practical consequences of the administration's accumulated debt-service disputes, including the long-running council officials' entitlements case.